I often hear the idiom "falling off the wagon", as in "Has Robert Downey Jr. fallen off the wagon?" (i.e. Is he drinking alcohol again?). Where did the phrase originate? What wagon? And why is being "on the wagon" synonymous with being sober?

6 Answers
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From The Encyclopedia of Word and Phrase Origins, by Robert Hendrickson:

The original version of this expression, 'on the water wagon' or 'water cart,' which isn't heard anymore, best explains the phrase. During the late 19th century, water carts drawn by horses wet down dusty roads in the summer. At the height of the Prohibition crusade in the 1890s men who vowed to stop drinking would say that they were thirsty indeed but would rather climb aboard the water cart to get a drink than break their pledges. From this sentiment came the expression 'I'm on the water cart,' I'm trying to stop drinking, which is first recorded in, of all places, Alice Caldwell Rice's Mrs. Wiggs of the Caggage Patch [1901], where the consumptive Mr. Dick says it to old Mrs. Wiggs. The more alliterative 'wagon' soon replaced cart in the expression and it was eventually shortened to 'on the wagon.' 'Fall off the (water) wagon' made its entry into the language almost immediately after its abstinent sister.

Now I know! Thanks very much. Can you clarify if this phrase originates in the US?
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Django ReinhardtAug 8 '11 at 2:11

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As far as I can tell, it did originate in the US. Alice Caldwell Rice, whose novel was cited as the first recorded use of the phrase, was an American novelist (also known as Alice Hegan Rice).
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NicholasAug 8 '11 at 2:35

Meaning

However, the saying is indeed originally American and it is associated with wagons, of a sort. The original form, which dates from the early years of the twentieth century, was to be on the water-wagon, implying that the speaker was drinking water rather than alcohol and so was an abstainer, at least for the time being. The image of the horse-drawn water-wagon would have been an obvious one at the time — it was used to spray unpaved American streets in the dry summer months to dampen down dust thrown up by the traffic. A direct link with the temperance movement — very active at the time — would seem probable, though I’ve not been able to establish this for sure.

Wagon

The OED say on the wagon is originally from the US and has it from a 1906 book by Bert Leston Taylor titled Extra Dry: being further adventures of the Water Wagon:

It is better to have been on and off the Wagon than never to have been on at all.

Charles Warner the English actor tells the following on himself: "A few nights after I reached New York I asked to have a drink. He replied: 'I am on the water wagon.' 'On the what?' I asked. He explained, and I thought it was a good one and resolved to spring it immediately. Two days later I met Mr. Hawtry and he asked me to join him a high ball. 'Sorry, old fellow,' I said, 'but I am on the washtub, don't you know?' Beastly blunder, but very English, was it not?"

Water cart

I'm on the water cart is claimed to have been first recorded in Alice Caldwell Rice's Mrs. Wiggs of the Caggage Patch (1901), but I found it in The Red Cloud Chief (Red Cloud, Webster Co., Neb., July 06, 1900) in "A Tragedy in Slums: Romance in the Low Life of New York":

She visited a few of her friends and confided to them she was going to get married.

Great answer, thanks! One thing: You don't actually explain where the phrase comes from (i.e. what is the wagon, and why would you be on it?). Nicholas's answer does a great job of that, even if, as you've proved, it incorrect in other areas.
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Django ReinhardtFeb 10 '13 at 1:55

Example: Dean Martin never fell off the wagon. You have to be on the wagon before you can fall off.

Origin: The origin of this seemingly mysterious phrase becomes clear when one learns that the original phrase was “On the water wagon”. A water wagon was a common piece of equipment in the days before paved roads. They were used to spray the dirt roads to help control dust.

Alternative: It dates to Victorian times when prisoners where transported to the Old Bailey on a wagon. The officers guarding them would stop for a drink but the prisoners would have to stay on the wagon.

Another origin: during the Temperance days, people repented their sins (often drinking) in evangelical churches and publicly declared themselves "on the water wagon" at town parades. The water wagon-- or any wagon that would hold a few people-- would be drawn along in a parade and the "repented sinners" would be on it. There would be some kind of identification-- repenting sinners etc-- and the idea was, you showed your self-reformation publicly so that other people could hold you to it.

If memory serves the opening scene of "The Wild Bunch" has a temperance wagon in it.

It is probably derived from the earlier idiom, "get on the bandwagon," which had just come into common use a few years earlier. The original form, "water wagon," may also have been a humorous alusion to "temperance wagons," (like Salvation Army wagons) that drove around cities preaching the gospel of abstinence. To be "on the water wagon" was to be "on the bandwagon" of abstaining from alcohol. To "fall off the water wagon" was to start drinking again.
The phrase dates to at least, 1896. It appeared in the book, Checkers, a Hard Luck Story. A bicycle salesman from Chicago may have coined the phrase.
http://esnpc.blogspot.com/2014/09/beer-wagons-water-wagons-temperance.html

the meaning dates back to the 1500's when prisoners were transported from the Tower of London down what is now Oxford st to be hung at the tyburn tree by marble arch. They were taken by cart and along the way they were given drinks by locals lining the street. By the time they'd reached half way they were often drunk and fell of the cart/wagon. Hence the expression